294677-67-1

Upstream product

• 69850-47-1 (2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol 
• 294677-66-0 2,3-di-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate 

Downstream Products

• 144174-64-1 methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside 
• 294677-68-2 Acetic acid (2S,3R,4R,5R,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester 
• 294677-70-6 methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-(4-O-benzyl-α-L-rhamnopyrnosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside 
• 294677-69-3 Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-4-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Synthesis of a trisaccharide and a tetrasaccharide from the cell-wall lipopolysaccharides of Azospirillum brasilense S17

A trisaccharide containing a D-mannosamine moiety and a tetrasaccharide containing an L-rhamnan chain that are found in the cell walls of Azospirillum brasilense S17 were synthesized concisely and in excellent yields. The key features of the synthetic str

Linear synthesis of the methyl glycosides of tri-, tetra-, and pentasaccharide fragments of the Shigella flexneri serotype 5a o-antigen1

The stepwise synthesis of methyl α-D-glucopyranosyl-(1-→3)-α-L-rhamnopyranosyl-(1-→3)-α-L-rhamnopyranoside (EBC-OMe, 1), methyl α-L-rhamnopyranosyl-(1 →2)-[α-D-glucopyranosyl-(1-→ 3)]-α-L-rhamnopyranosyl-(1-→ 3)-α-L-rhamnopyranoside (A(E)BC-OMe, 2), and methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-→2)-α-L-rhamnopyranosy l-(1-→ 2)-[α-D-glucopyranosyl-(1- 3)]-α-L-rhamnopyranosyl-(1-→3)-α-L-rhamnopyranoside (DA(E)BC-OMe, 3) is described. Compounds 1, 2 and 3 constitute the methyl glycosides of fragments of the O-specific polysaccharide of Shigella flexneri serotype 5a. Methyl 2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1-→3)-2,4-di-O-benzoyl-α- L-rhamnopyranoside was an appropriate BC precursor for the synthesis of 1. For the synthesis of the branched targets 2 and 3, a benzyl group was best suited at position 2 of rhamnose C. Thus, methyl 4-O-benzyl-α-L-rhamnopyranosyl-(1-→3)-2,4-di-O-benzyl-α-L-rhamn opyranoside was the key intermediate to the BC portion. In all cases, 2,3,4,6-tetraO-benzyl-α-D-glucopyranosyl fluoride was a convenient E precursor, when used in combination with titanium tetrafluoride. All along, attention was paid to steric hindrance as a factor of major impact on the condensation steps outcome. Therefore, based on previous experience, 2-O-acetyl-3,4-di-O-allyl-α-L-rhamnopyranosyl trichloroacetimidate and 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl trichloroacetimidate were used as donors. Both suited all requirements when used as key precursors for residues A and D in the synthesis of 3, respectively.